Structure of 25365-71-3
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 25365-71-3 |
Formula : | C15H11NO |
M.W : | 221.25 |
SMILES Code : | O=CC1=C(C2=CC=CC=C2)NC3=C1C=CC=C3 |
MDL No. : | MFCD00435481 |
InChI Key : | IFIFXODAHZPTEY-UHFFFAOYSA-N |
Pubchem ID : | 613305 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With triethylamine; In N,N-dimethyl-formamide; at 80 - 90℃; for 0.75h; | General procedure: To a suspension of the iminium salt prepared as above from the proper indole, a solution of suitable active methylene reagent (11mmol) and triethylamine (1.21g, 12mmol) in dry DMF (8mL), pre-warmed to 80C, was added in one portion. The reaction mixture was stirred for 45min at 90C (for 13b: 1.5h at 105C). After cooling to rt, Et3N·HCl precipitated and the resulting suspension was treated with water (50mL). Then, work-ups 1-4 were carried out, as follows: (0038) Work-up 1 (for 9a, i, j, n, o; 10j; 12a, i; 13a-d, f, i-k, m, o; 14a, j; 15a, j; 16a, j): the suspension was allowed to stand for 2h. The precipitate obtained was filtered off, air dried and purified by crystallization. (0039) Work-up 2 (for 12n; 13e): the precipitate was filtered off and dissolved in CH2Cl2. The organic layer was washed with water (3×20mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the solvent, the crude product was purified by crystallization from ethanol. (0040) Work-up 3 (for 12j; 13h): the precipitate was filtered off, air dried, purified by chromatography (eluents: petroleum ether/ethyl acetate) and then crystallized from CHCl3 and diethyl ether (12j) or ethyl acetate mixture (13h). (0041) Work-up 4 (for 9g; 10i; 11j; 13l, n): the reaction mixture was extracted with ethyl acetate (9g; 10i; 11j) or CH2Cl2 (13l, n) (3×35mL). The combined organic extracts were washed with water (5×30mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the filtrate, the crude products 10i and 13l were crystallized from the proper solvent(s). Conversely, the crude products 9g and 13n were purified by chromatography (eluent: petroleum ether/ethyl acetate) and then crystallized from the proper solvent mix. For 11j, the filtrate was extracted with 1N HCl (10mL×2), the organic layer (CH2Cl2) was separated and discarded, while the acid aqueous phase was made alkaline with 1N NaOH (25mL) and extracted with dichloromethane. The combined organic extracts were washed with water (2×20mL), dried over anhydrous Na2SO4 and evaporated in vacuo: the residue was crystallized from acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | 2-Phenylindole-3-carboxaldehyde (300 mg, 1.36 mmol) and NaBH4 (103 mg, 2.72 mmol) were stirred at reflux in ethanol (10 mL) for 1 min followed by stirring at room temperature for 2 h. 1% NaOH (10 mL) was added to the reaction mixture and the product was extracted with Et2O (3 × 10 mL). The combined extracts were dried (MgSO4), filtered and the solvent evaporated to yield a crude product which was re-crystallised in PhMe: EtOAc:petroleum ether, yielding the title compound as a white solid 133 mg, 44%). (0029) 1H NMR (250 MHz, DMSO-d6) δH 4.81 (d, J = 5.0 Hz, 2H), 5.10 (t, J = 5.0 Hz, 1H), 7.14-7.28 (m, 2H), 7.48-7.53 (m, 2H), 7.64 (t, J = 7.5 Hz, 2H), 7.80 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 7.5 Hz, 2H), 11.47 (s, 1H); 13C NMR (62.5 MHz, DMSO-d6), δC 54.8, 112.1, 113.3, 119.9, 122.6. 128.5, 128.9, 129.67, 129.71, 133.4, 136.8, 136.9; νmax (film, cm-1) 3488, 3183 (br s), 1638, 1491, 1452, 1392; m/z (CI) 206 ([M-OH]+, 100%) | |
44% | With sodium tetrahydroborate; ethanol; at 20℃; for 2.02h;Reflux; | 2-Phenylindole-3-carboxaldehyde (300 mg, 1.36 mmol) and NaBH4 (103 mg, 2.72 mmol) were stirred at reflux in ethanol (10 mL) for 1 minute followed by stirring at room temperature for 2 hours. 1 % NaOH (10 mL) was added to the reaction mixture and the product was extracted with Et20 (3 x 10 mL). The combined extracts were dried (MgS04), filtered and the solvent evaporated to yield a crude product which was re-crystallised in PhMe:EtOAc:petroleum ether, yielding the title compound as a white solid 133 mg, 44%). 1 H NMR (250 MHz, DMSO-d6) δΗ 4.81 (d, J = 5.0 Hz, 2H), 5.10 (t, J = 5.0 Hz, 1 H), 7.14-7.28 (m, 2H), 7.48-7.53 (m, 2H), 7.64 (t, J = 7.5 Hz, 2H), 7.80 (d, J = 7.5 Hz, 1 H), 7.92 (d, J = 7.5 Hz, 2H), 1 1.47 (s, 1 H); 13C NMR (62.5 MHz, DMSO-d6), 5C 54.8, 1 12.1 , 1 13.3, 1 19.9, 122.6. 128.5, 128.9, 129.67, 129.71 , 133.4, 136.8, 136.9; vmax (film, cm 1) 3488, 3183 (br.), 1638, 1491 , 1452, 1392; m/z (C) 206 ([M-OH]+, 100% |
19% | With sodium tetrahydroborate; In ethanol; at 20℃; for 2.01667h;Reflux; | 2-Phenylindole-3-carboxaldehyde (1.00 g, 4.52 mmol) and NaBH4 (0.34 g, 9.04 mmol) were added to ethanol (34 mL) and heated at reflux for 1 minutes followed by stirring at room temperature for 2 hours. NaOH (1%, 35 mL) was added, and the solvent was removed in vacuo. The reaction was extracted with Et2O (3 × 30 mL), dried (MgSO4), filtered and the solvent removed in vacuo. Due to the title compound being degraded on silica, the reaction was purified by recrystallization (EtOAc, few drops of PE) to yield the product as a white solid (187 mg, 19% yield). Rf = 0.21 (5:2 petroleum ether: ethyl acetate); 1H NMR (300 MHz, DMSO): δH = 11.35 (1 H, s, NH), 7.79 (2H, m, Ar), 7.66 (1 H, d, J = 7.5 Hz, Ar), 7.52 (2 H, t, J = 7.5 Hz, Ar), 7.35-7.44 (2 H, m, Ar), 7.12 (1 H, td, J = 7.5 Hz, 1.0 Hz, Ar), 7.03 (1 H, td, J = 7.5, 1.0 Hz, Ar), 4.96 (1 H, t, J = 5.0 Hz, OH), 4.67 (2 H, d, J = 5.0 Hz, CH2); 13C NMR (75 MHz, DMSO): δC = 135.94 (Ar, Cq), 135.82 (Ar, Cq), 132.41 (Ar, Cq), 128.74 (Ar, Cq), 128.71 (Ar, CH), 127.97 (Ar, CH), 127.57 (Ar, CH), 121.62 (Ar, CH), 118.94 (Ar, CH), 112.35 (Ar, Cq), 111.13 (Ar, CH), 53.86 (CH2); MS (ESI): m/z 206 ([M-OH]+ ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With silica supported ceric ammonium nitrate; In acetonitrile; for 12h;Reflux; | General procedure: a mixture of indole (1 mmol), HMTA (2.5 mmol), and 10% CAN-SiO2 was refluxed in CH3CN (5.0 mL). After the reaction was complete, the mixture was evaporated to give a crude residue of CAN-SiO2 and product. The crude residue was washed with EtOAc (10 mL 5) and dried to leave a crude product that was purified by short flash column chromatography (EtOAc/hexane = 1:3). |
77% | With aluminum (III) chloride; In N,N-dimethyl-formamide; at 120℃; for 2h; | General procedure: A method for synthesizing compound III-1 wherein R1, R2 and R3 are simultaneously hydrogen in the formula III, the method comprising the steps of:(1) Add to a 50 mL round bottom flask1.0mmol indole(In the formula I, R1, R2, and R3 are both hydrogen) and1.0 mmol (0.140 g) of hexamethylenetetramine, then 2 mL of N,N-dimethylformamide (DMF), stirred in a magnetic stirrer to dissolve the solid, followed by the addition of 0.05 mmol (0.012 g) of crystalline trichloride Aluminum, connected to a reflux condenser, heated at 120 C, the reaction progress was monitored by TLC, and the reaction was cooled to room temperature after 1 h to prepare a suspension;(2) The suspension prepared in the step (1) is suction filtered with a funnel padded with diatomaceous earth.The filter cake was washed well with ethyl acetate, suction filtered, and the above operation was repeated until the filtrate had no product, and all the filtrates were combined.Dilute with 15 mL of saturated saline solution, disperse and separate the layers, and the aqueous layer was further extracted with ethyl acetate three times.Each time 10 mL, the ethyl acetate layer was combined and washed with 10 mL of 2 mol/L diluted hydrochloric acid.Wash with 10 mL of saturated sodium bicarbonate solution, and finally wash with 10 mL of saturated brine.The washed ethyl acetate layer was dried over anhydrous sodium sulfate, and after drying, the desiccant was filtered off.Then use a rotary evaporator to recover the solvent to concentrate the product, and finally,The residue is subjected to silica gel column chromatography using a mixture of n-hexane-ethyl acetate (V/V = 2:1) as an eluent to obtain a purified product.The mass of the compound III-indole-3-carbaldehyde is 0.137g,The product yield was 94%. |
70% | With iodine; oxygen; pyrographite; In N,N-dimethyl-formamide; at 120℃; for 4h; | General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I2 (0.2 mmol, 0.0507g, 20 mol%) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO3 solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product. |
65% | With water; iodine; In N,N-dimethyl-formamide; at 150℃; under 5171.62 Torr; for 0.133333h;Flow reactor; | General procedure: The continuous flow reactor system consisted of the dual pump (KP-22-13, SS), PTFE tubing (length: 16 m, ID: 1 mm), T-junction (1.25 mm thru-hole), back pressure regulator (40, 75, 100, 250 psi), oil bath and hot plate. In this experiment, we used BOLA PTFE tubing to experiment at high temperature. In order to react stably at the temperature above the boiling point of water, looked for the maximum temperature conditions according to the pressure of the back pressure regulator in which the bubble does not occur. The reaction started in the concentration of indole (1.0 mmol), HMTA (2.0 mmol) and I 2 (1.0 mmol) in solvent (10 mL). Since this reaction proceeds in a single phase of liquid, the reaction time was set by the inner volume of tubing and the flow rate in the continuous flow reactor. After the reaction is over, the product was quantified using 1 H NMR and the NMR yield was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 4 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4. The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system. | |
89% | With trichlorophosphate; at 70℃;Inert atmosphere; | General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 3 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4.The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system [27]. 2-Phenyl-1H-indole-3-carbaldehyde (4a). Cream powder; Mp: 249-250 C; Yield: 89%; IR (KBr, cm-1): 3144 (NH), 2858(H-CO), 1625 (C=O), 1455 (C=C). 1H NMR (500 MHz, DMSO-d6) (δ, ppm): 7.24 (t, J = 7.9 Hz, 1H, H6), 7.29 (t, J = 7.9 Hz, 1H, H7), 7.51 (d, J = 7.9 Hz, 1H, H8), 7.56-7.62 (m, 3H, H3′,5′,4′), 7.78 (d, J = 9.3 Hz, 2H, H2′,6′), 8.21 (d, J = 7.9 Hz, 1H, H5), 9.96 (s, 1H, CHO), 12.40 (s, 1H, NH-indole). 13C NMR (125 MHz, DMSO-d6) (δ, ppm): 112.1, 113.5, 121.2, 122.5, 123.7, 125.8, 128.9, 129.2, 129.8, 130.1,135.9, 149.1, 185.5. Anal. Calcd. for C15H11NO: C, 81.43; H, 5.01; N, 6.33. Found: C, 81.53; H, 4.85; N, 6.45. |
88% | With trichlorophosphate; at 10 - 45℃; for 0.5h; | General procedure: Compounds 10a-f were synthesized by known procedure. A solution of 2-aryl-1H-indole 9a-f (0.01 mol) in a minimum amount of DMF was added to the Vilsmeier-Haack reagent (was prepared from phosphorus oxychloride (1 mL) and DMF(3.15 mL)) maintaining the reaction temperature between 10 and 20 C. The reaction mixture was heated at 45 C for 30 min and poured into a mixture of ice-water (100 mL) and 10% aqueous NaOH (20 mL). The resulting mixture was refl uxed for 1 h and cooled to room temperature. The precipitate was collected by filtration, washed with water, dried, and recrystallized. 2-Phenyl-1H-indole-3-carbaldehyde (10a). White substance,yield 194 mg (88%), m.p. 236-240 C (dioxane) (cf. Ref. 33:m.p. 249-250 C). 1H NMR (DMSO-d6), δ: 7.41-7.21 (m, 2 H,H(5), H(6)); 7.52 (d, 1 H, H(7), J = 7.9 Hz); 7.67-7.56 (m, 3 H,H(3), H(4), H(5)); 7.85-7.76 (m, 2 H, H(2), H(6)); 8.23(d, 1 H, H(4), J = 7.5 Hz); 9.98 (s, 1 H, CHO); 12.43 (s, 1 H,NH). 13C NMR (DMSO-d6), δ: 112.5 (C(3)), 113.9 (C(7)),121.5 (C(5)), 122.9 (C(6)), 124.2 (C(4)), 126.2 (C(2)), 129.5(2 C, C(2), C(6)); 130.2 (C(3a)), 130.3 (C(4)), 130.4 (2 C, C(3),C(5)); 136.4 (C(1)), 149.6 (C(7a)), 186.0 (CHO). MS (ESI), m/z:244.0731 [M + Na]+. C15H11NNaO. Calculated: M = 244.0733. |
78% | General procedure: Into a 25 mL tube, Ph3P (0.75 mmol, 1.5 equiv.), ICH2CH2I (0.75 mmol, 1.5 equiv.)indoles 1 (0.5 mmol, 1 equiv.), DMAP (0.5 mmol, 1 equiv.), and DMF (2 mL) wereadded under air atmosphere. The resulting mixture was stirred at 80 oC for 2 hours. H2O(5 mL) was added and stirred at 80 oC for another 2 hours. The mixture was cooled toroom temperature. A saturated aqueous brine solution was added, and the crude organicproduct was extracted by CH2Cl2. The combined organic phase was dried withanhydrous Na2SO4. After filtration, the solution was concentrated under reducedpressure to remove the solvent. The residue was subjected to flash columnchromatography on silica gel (pentane/ethyl acetate) to give the pure pro ducts 4j-4u. | |
[0271] A mixture of DMF (11.0 mL, 142 mmol) and phosphorous oxychloride (3.63 mL, 39 mmol) is stirred at 0 C. for 1 h, a 0.2 mL portion is pipetted into a solution of 2-phenylindole (96 mg, 0.5 mmol) in DMF at 5 C. This reaction mixture is stirred at 5-10 C. for 1 h, quenched with water, stored at -200 for 16 h and filtered. The filtercake is washed with water and dried in vacuo to afford the 2-phenylindole-3-carboxaldehyde intermediate. A suspension of the thus-obtained 2-phenylindole-3-carboxaldehyde (44.2 mg, 0.2 mmol) in isopropanol and concentrated HCl (50 μL) is treated with aminoguanidine bicarbonate (27 mg, 0.2 mmol), heated at 80 C. for 2 h, cooled to room temperature and concentrated in vacuo. The resultant residue is purified by HPLC to afford the title product, 28 mg (20% yield), identified by mass spectral and HPLC analyses (M+H) 277; retention time 3.76 min. 1HPLC conditions: Hewlett Packard 1100; YMC ODS-A 4.6 mm×50 mm 5 u column at 23 C.; 10 uL injection; Solvent A: 0.05% TFA/water; Solvent B: 0.05% TFA/acetonitrile; Gradient: Time 0: 98% A; 1 min: 98% A; 7 min: 10% A, 8 min: 10% A; 8.9 min: 98% A; Post time 1 min. Flow rate 2.5 mUmin; Detection: 220 and 254 nm DAD. | ||
General procedure: P-substituted acetophenone (2mmol) and phenyl-hydrazine (2mmol) were poured into a round bottom flask, then CH3COOH (0.5mL) and CH4O3S (27mmol) were added. After the thin layer chromatography (TLC) monitoring reaction was completed, the intermediate 3 was obtained by pouring the mixture into ice water. At -30C, POCl3 (10mmol) was slowly added dropwise to a round bottom flask containing DMF (10mmol), and the reaction was stirred for 1h. After that, intermediate 3 (1mmol) was dissolved in DMF, slowly added dropwise to the flask, and the reaction was heated to 70C with stirring. Monitor the reaction through the TLC. Finally, the mixture was poured into ice water, washed with 40% NaOH solution, and then extracted with DCM to obtain intermediate 4. | ||
With Vilsmeier reagent; trichlorophosphate; at 0℃; for 2h; | Compound 4 (5.5mmol, 1eq) was added to the Vilsmeier-haack reagent prepared by the addition of POCl3 (3.8eq) in DMF (5.1mmol of 4) at 0C. The mixture was stirred at 0C for 2 hrs to ensure the complete consumption of starting material by TLC monitoring. Then reaction was quenched slowly by adding ice and neutralized the reaction mixture by adding the 37% of NaOH solution. The resulting precipitate was filtered and dried to afford the 2-Phenylindole-3-carboxaldehyde (5) in good yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | A solution of 2-phenylindole-3-carboxyaldehyde (1 g, 4.52 mmol) with sodium hydride (60% in oil, 0.36 g, 9 mmol) in dry THF (20 mL) was stirred at room temperature for 30 mins. Acetic anhydride (1.27 mL, 13.5 mmol) was added and stirred for a further 3 hours until the reaction was complete by TLC. The crude reaction was quenched with the addition of water (1 mL) dropwise. The reaction was diluted with water (30 mL), and was extracted with ethyl acetate (2 × 15 mL). The organic phase was dried (MgSO4), filtered and concentrated in vacuo, and purified by flash column chromatography on silica gel (10:1 petroleum ether: ethyl acetate) to yield 1-acetyl-<strong>[25365-71-3]2-phenyl-1H-indole-3-carbaldehyde</strong> (1.07 g, 90% yield). Rf = 0.57 (2:1 petroleum ether: ethyl acetate); 1H NMR (300 MHz, CDCl3): δH = 9.76 (1H, s, CHO), 8.44 - 8.37 (1H, m, Ar), 8.33 - 8.25 (1H, m, Ar), 7.63 - 7.52 (5H, m, Ar), 7.50 - 7.38 (2H, m, Ar), 2.03 (3H, s, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With acetic acid; for 1h;Reflux; | The mixture of equimolar quantities of 6-phenylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (3) or 2-aryl-1H-indole-3-carbaldehyde (1.0 eq.) and thiosemicarbazide (1.0 eq.) in the acetic acid was heated under reflux for 1h. After the reaction mixture was cooled to the room temperature, formed precipitate was filtered off, washed with acetic acid, water and ethanol and recrystallized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.3% | Synthesis of other indole-3-carbaldehydes; Preparation of 1-methyl-2-phenyl-1 H-indole-3-carbaldehyde: To a solution of 2-phenyl-1 H-indole-3-carbaldehyde (7.41 g, 33.5 mmol) in DMF (50 ml) cooled to O0C was added in portions, sodium hydride (2.68 g, 67.0 mmol). After stirring for 30 minutes, iodomethane (4.18 ml, 67.0 mmol) was added and the reaction stirred for 30 minutes, then allowed to warm to room temperature and stirred overnight. Water (150 ml_) was added and the resulting solid was filtered, washed well with water and air dried to give a light green solid 1-methyl-2-phenyl-1 H-indole-3-carbaldehyde (5.30 g, 22.53 mmol, 67.3 % yield), MS (m/z) 236.3 (MH+). | |
With potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 12h; | Step 2: In a 500 ml flask provided with a cooling tube and a stirrer, 15.2 g of KOH, 38 g of iodomethane, 50 g of 2-phenyl 1H-Indole-3-carboxaldehyde, and 150 g of DMF (dimethylformamide) were placed and stirred at room temperature for 12 hours. The solvent was removed through distillation, thereby obtaining 1-methyl 2-phenyl 1H-indole-3-carboxaldehyde (molecular weight: 235.28 g/mol) and having a purity of 96% as measured by HPLC. (1H NMR: δ 9.76, s, 1H; δ 8.46, m, 1H; δ 7.59, m, 3H; δ 7.52, m, 2H; δ 7.42, m, 3H; δ 3.79, s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine;Reflux; | General procedure: A mixture of 2-Phenylindole-3-carboxaldehyde (1g, 4.51mmol, 5), acetophenone (0.5mL, 4.51mmol, 6) and piperidine (1.8mL) was taken in a well-dried round bottom flask and heated for 2-4 hrs, then ethanol (7mL), glacial acetic acid and water (1:1) were added to resulting red solution until first appearance cloudiness. The progress of the reaction is monitored by TLC. The resulting product was filtered off and washed with water, dried to afford the desired product (7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dmap; triethylamine; In dichloromethane; at 20℃; for 0.416667h;Inert atmosphere; | General procedure: To a solution of indole-3-carboxaldehyde, triethylamine (1.3 equiv.), and 10 mol % DMAP in CH2Cl2 was added Boc2O (1.2 equiv.). The reaction was stirred at room temperature until the starting material was completely consumed. The reaction was diluted with CH2Cl2, worked up with water. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EA/nHx =1:5 for 1a, 1b; EA/nHx = 1:9 for 1c) to give compounds 1a-1c. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | 1.7 g of POCl3 was added drop wise to a solution of 2-phenyindole (1.93 g) in 20 mL of DMF, at 10 C. The mixture was stirred at 50 C. for 1 hr, cooled and diluted with saturated NaHCO3. The suspension was heated at 60 C. for 15 min, cooled, the precipitates of 2-phenylindol-3-carboxaldehyde were filtered. Yield 2.05 g (93%). The mixture of phenanthroquinoline (0.105 g) and 2-phenylindol-3-carboxaldehyde (0.111 g) was refluxed in 3 mL of acetic acid in the presence of 0.39 g of ammonium acetate for 1.5 hrs. The red colored solution was poured in water (100 ml) and washed with DCM (3×40 ml). The aqueous layer was then neutralized with saturated aqueous solution of NA2CO3, the solid obtained was filtered, washed with EtOH and crystallized from DMF: EtOH:H2O=1:1:1. A purified solid 0.12 g was achieved, with a yield of 58%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With hydrogenchloride; In water; isopropyl alcohol; at 80℃; for 2h; | [0271] A mixture of DMF (11.0 mL, 142 mmol) and phosphorous oxychloride (3.63 mL, 39 mmol) is stirred at 0 C. for 1 h, a 0.2 mL portion is pipetted into a solution of 2-phenylindole (96 mg, 0.5 mmol) in DMF at 5 C. This reaction mixture is stirred at 5-10 C. for 1 h, quenched with water, stored at -200 for 16 h and filtered. The filtercake is washed with water and dried in vacuo to afford the <strong>[25365-71-3]2-phenylindole-3-carboxaldehyde</strong> intermediate. A suspension of the thus-obtained <strong>[25365-71-3]2-phenylindole-3-carboxaldehyde</strong> (44.2 mg, 0.2 mmol) in isopropanol and concentrated HCl (50 μL) is treated with aminoguanidine bicarbonate (27 mg, 0.2 mmol), heated at 80 C. for 2 h, cooled to room temperature and concentrated in vacuo. The resultant residue is purified by HPLC to afford the title product, 28 mg (20% yield), identified by mass spectral and HPLC analyses (M+H) 277; retention time 3.76 min. 1HPLC conditions: Hewlett Packard 1100; YMC ODS-A 4.6 mm×50 mm 5 u column at 23 C.; 10 uL injection; Solvent A: 0.05% TFA/water; Solvent B: 0.05% TFA/acetonitrile; Gradient: Time 0: 98% A; 1 min: 98% A; 7 min: 10% A, 8 min: 10% A; 8.9 min: 98% A; Post time 1 min. Flow rate 2.5 mUmin; Detection: 220 and 254 nm DAD. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; isopropyl alcohol; | EXAMPLE 3a Hydrolysis of 2-(2-phenylindol-3-yl)-1,3-diphenyl imidazolidine 4.0 parts by weight of 2-(2-phenylindol-3-yl)-1,3-diphenyl imidazolidine are suspended in 10 parts by volume of isopropanol and 4 parts by volume of 10% aqueous hydrochloric acid added. Thereafter water is added and 1.7 parts by weight of 3-formyl-2-phenyl indole are obtained by filtering off. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
piperidine; In ethanol; | Example 33 (General Procedure (G)) 2-(2-Phenyl-3-Indolylmethylene)-Malononitrile. The title compound was prepared from 2-phenyl-3-formylindole and malonitrile in ethanol using a catalytic amount of piperidine. 1H NMR (400 MHz, CHLOROFORM-D): δ ppm 7.40 (m, 2 H) 7.49 (m, 3 H) 7.60 (m, 3 H) 7.81 (s, 1H) 8.25 (m, 1H) 9.02 (s, 1H); HPLC-MS (Method A): mlz=270 (M+1); Rt=4.72 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; triethylamine; In ethanol;Reflux; | General procedure: Compounds 11a-f and 13a,b were synthesized by the earlier described modified procedure. A 5-mL round bottom flask was charged with 2-aryl-1H-indole-3-carbaldehyde 10a-f or 12a,b (1 mmol), hydroxylamine hydrochloride (0.207 g, 3 mmol), triethylamine (0.3 mL, 3 mmol), and EOH (2 mL). The mixture was refluxed for 1-2 h (TLC monitoring). After reaction completion, the solvent was removed in vacuo, the residue was dissolved in ethylacetate (20 mL), and washed with water (3×15 mL). The combined organic layers were dried and concentrated in vacuo. The products were obtained in quantitative yields. Compounds 11a-f and 13a,b were used in the next step without purification; if necessary, they can be purified by silica gel columnchromatography (gradient elution with ethyl acetate-hexane,1 : 8→1 : 4). 2-Phenyl-1H-indole-3-carbaldehyde oxime (11a). Whitesubstance, m.p. 179.2-183.1 C. 1H NMR (DMSO-d6), δ: 7.13(t, 1 H, H(5), J = 7.5 Hz); 7.21 (t, 1 H, H(6), J = 7.5 Hz); 7.43(d, 1 H, H(7), J = 8.0 Hz); 7.48 (t, 1 H, H(4), J = 6.9 Hz);7.54-7.64 (m, 4 H, H(2), H(3), H(5), H(6)); 8.08 (d, 1 H,H(4), J = 7.9 Hz); 8.26 (s, 1 H, CH=N); 10.72 (s, 1 H, NH);11.76 (s, 1 H, OH). 13C NMR (DMSO-d6), δ: 105.8 (C(3)),111.5 (C(7)), 120.5 (C(5)), 121.9 (C(6)), 122.8 (C(4)), 125.5(C(2)), 128.6 (C(4)), 129.0 (4 C, C(2), C(3), C(5), C(6));131.3 (C(3a)), 136.0 (C(1)), 139.7 (C(7a)), 144.3 (CH=N).MS (ESI), m/z: 237.1026 [M + H]+. C15H13N2O. Calculated:M = 237.1022. Rf 0.22 (EtOAc-hexane, 1 : 4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With ammonium acetate; In acetic acid; for 1.5h;Reflux; | 1.7 g of POCl3 was added drop wise to a solution of 2-phenyindole (1.93 g) in 20 mL of DMF, at 10 C. The mixture was stirred at 50 C. for 1 hr, cooled and diluted with saturated NaHCO3. The suspension was heated at 60 C. for 15 min, cooled, the precipitates of 2-phenylindol-3-carboxaldehyde were filtered. Yield 2.05 g (93%). The mixture of phenanthroquinoline (0.105 g) and 2-phenylindol-3-carboxaldehyde (0.111 g) was refluxed in 3 mL of acetic acid in the presence of 0.39 g of ammonium acetate for 1.5 hrs. The red colored solution was poured in water (100 ml) and washed with DCM (3×40 ml). The aqueous layer was then neutralized with saturated aqueous solution of NA2CO3, the solid obtained was filtered, washed with EtOH and crystallized from DMF: EtOH:H2O=1:1:1. A purified solid 0.12 g was achieved, with a yield of 58%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In ethanol;Reflux; | General procedure: A mixture of 2-Phenylindole-3-carboxaldehyde (1g, 4.51mmol, 5), acetophenone (0.5mL, 4.51mmol, 6) and piperidine (1.8mL) was taken in a well-dried round bottom flask and heated for 2-4 hrs, then ethanol (7mL), glacial acetic acid and water (1:1) were added to resulting red solution until first appearance cloudiness. The progress of the reaction is monitored by TLC. The resulting product was filtered off and washed with water, dried to afford the desired product (7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With rochelle salt; In neat (no solvent); for 0.0666667h;Microwave irradiation; Molecular sieve; Green chemistry; | General procedure: A mixture of equivalent amounts of 2,5-disubstituted indole-3-carboxaldehyde with malononitrile, dimedone, thiobarbutiric acid or barbutiric acid (1 mmol each) and KNaC4H4O6*4H2O (10 mol %) was mixed with finely powdered 5 Å Molecular sieve (0.5-1.0 g) and loaded into an open borosil glass vessel. The mixture was subjected to MW-irradiationat power of 350-450 W for 8-10 min upon heating to 125-150 C followed by the procedure as reported earlier [6, 23]. |
A617373 [590391-01-8]
1H-Indole-3-carboxaldehyde, 2-(3,4-dimethylphenyl)-
Similarity: 1.00
A415195 [68945-00-6]
2-(p-Tolyl)-1H-indole-3-carbaldehyde
Similarity: 1.00
A927826 [94210-62-5]
2-(Naphthalen-2-yl)-1H-indole-3-carbaldehyde
Similarity: 1.00
A488704 [590390-99-1]
2-(2,4-Dimethylphenyl)-1H-indole-3-carbaldehyde
Similarity: 0.98
A550026 [92855-23-7]
7-Methyl-2-phenyl-1H-indole-3-carbaldehyde
Similarity: 0.98
A617373 [590391-01-8]
1H-Indole-3-carboxaldehyde, 2-(3,4-dimethylphenyl)-
Similarity: 1.00
A415195 [68945-00-6]
2-(p-Tolyl)-1H-indole-3-carbaldehyde
Similarity: 1.00
A927826 [94210-62-5]
2-(Naphthalen-2-yl)-1H-indole-3-carbaldehyde
Similarity: 1.00
A243327 [590391-00-7]
2-(2,5-Dimethylphenyl)-1H-indole-3-carbaldehyde
Similarity: 0.98
A488704 [590390-99-1]
2-(2,4-Dimethylphenyl)-1H-indole-3-carbaldehyde
Similarity: 0.98
A617373 [590391-01-8]
1H-Indole-3-carboxaldehyde, 2-(3,4-dimethylphenyl)-
Similarity: 1.00
A415195 [68945-00-6]
2-(p-Tolyl)-1H-indole-3-carbaldehyde
Similarity: 1.00
A927826 [94210-62-5]
2-(Naphthalen-2-yl)-1H-indole-3-carbaldehyde
Similarity: 1.00
A488704 [590390-99-1]
2-(2,4-Dimethylphenyl)-1H-indole-3-carbaldehyde
Similarity: 0.98
A550026 [92855-23-7]
7-Methyl-2-phenyl-1H-indole-3-carbaldehyde
Similarity: 0.98